Arrowhead Report

Chiefs' Finale Is Reunion for Former AFC North Quarterbacks

Chris Oladokun, Kenny Pickett have taken different but equally winding football journeys.
May 26, 2022; Pittsburgh, PA, USA; Pittsburgh Steelers quarterback Chris Oladokun (5) participates in organized team activities at UPMC Rooney Sports Complex. Mandatory Credit: Charles LeClaire-Imagn Images
May 26, 2022; Pittsburgh, PA, USA; Pittsburgh Steelers quarterback Chris Oladokun (5) participates in organized team activities at UPMC Rooney Sports Complex. Mandatory Credit: Charles LeClaire-Imagn Images | Charles LeClaire-Imagn Images

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KANSAS CITY, Mo. – One player rode a roller coaster from team to team during college, then patiently waited nearly four full seasons with the same NFL organization for his first opportunity.

The other was a fixture at one college for five years, then rode a roller coaster through three teams over his first four NFL seasons.

Watch Chris Oladokun discuss below...

Chris Oladokun and Kenny Pickett are likely to start for their respective teams when Kansas City visits Las Vegas on Sunday (3:25 p.m. CT, CBS/KCTV, Channel 5, 96.5 The Fan). And after all they’ve been through, their first NFL summer together in Pittsburgh seems like generations ago.

For one, the Chiefs’ quarterback is finally dirtying a practice uniform during the regular season.

“I mean, physically, it definitely feels different,” said Oladokun, who’ll make his second NFL start Sunday. “I'm actually out there breaking a sweat a little bit, so that's definitely different. But I mean, I'm obviously, even in the meeting rooms, I've always prepared. Any play, I can play.

chris oladoku
South Dakota State quarterback Chris Oladokun throws a pass during a game against Southern Illinois on Saturday, October 9, 2021, at Dana J. Dykhouse Stadium in Brookings. | Erin Bormett / Argus Leader / USA TODAY NETWORK

“And so, my preparation hasn't changed from that standpoint. But physically, yes, you're definitely taking all the reps and you're in there.”

He wasn’t getting all the reps as a rookie. Far from it. Stuck in a quarterback room that included former No. 2-overall selection Mitchell Trubisky and Pickett, the 20th overall choice in that 2022 draft, Oladokun didn’t see many snaps.

pickett oladoku
May 13, 2022; Pittsburgh, PA, USA; Pittsburgh Steelers quarterbacks coach Mike Sullivan i(left) instructs quarterbacks Kenny Pickett (8) and Chris Oladokun (5) in drills during Rookie Minicamp at UPMC Rooney Sports Complex. Mandatory Credit: Charles LeClaire-Imagn Images | Charles LeClaire-Imagn Images

From Pittsburgh to Kansas City

After taking him in the seventh round of that ’22 draft, Pittsburgh cut Oladokun in the final roster reduction. Oladokun felt like he took a baseball bat in the stomach, until the Chiefs called a few days later.

“The first person to call me was Matt Nagy,” Oladokun recalled Wednesday. “I had already built a relationship a little bit with them, through the pre-draft process, and so I was familiar with them. Obviously loved Kansas City, and they seemed to like me.

“And when he called me, he's like, ‘Hey, what do you think about being a Chief?’ And that was something that I sort of always envisioned.”

kenny picket
Dec 14, 2025; Philadelphia, Pennsylvania, USA; Las Vegas Raiders quarterback Kenny Pickett (15) against the Philadelphia Eagles at Lincoln Financial Field. Mandatory Credit: Eric Hartline-Imagn Images | Eric Hartline-Imagn Images

He’s envisioning something else this week as he prepares to meet his former Steelers teammate: His first NFL victory.

“Yeah, it'd be huge,” Oladokun said. “I mean, at the end of the day, it's an AFC West opponent. It's a rivalry game versus the Raiders. And so, both teams are going to come out swinging. Obviously, the narrative is that the Raiders are going to lay down because they want the No. 1 pick. That's not going to happen.

“The Raiders are going to come out there and play really hard. Their defense is really good. I think they have a really good DC, Patrick Graham, so none of us expect them to lay down and we're both going to be playing to win.”

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Zak Gilbert
ZAK GILBERT

Since his freshman year at the University of Colorado, Zak Gilbert has worked 30 years in sports, including 18 NFL seasons. He's spent time with four NFL teams, serving as head of communications for both the Raiders and Browns. A veteran of nine Super Bowls, he most recently worked six seasons in the NFL's New York league office. He now serves as the Kansas City Chiefs Beat Writer On SI

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